Cyclohexanedionecarboxylic acid derivatives with herbicidal and plant growth regulating properties

ABSTRACT

Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR 2  or --NR 3  R 4  radical, 
     R is C 3  -C 6  cycloalkyl, 
     R 2 , R 3  and R 4  are each independently hydrogen, C 1  -C 6  alkyl, C 1  -C 6  haloalkyl, C 2  -C 10  alkoxyalkyl, C 2  -C 10  alkylthioalkyl; C 3  -C 6  alkenyl which is unsubstituted or substituted by halogen, C 1  -C 4  alkoxy or C 1  -C 4  alkylthio; C 3  -C 6  alkynyl; phenyl or C 1  -C 6  aralkyl, wherein the phenyl nucleus is unsubstituted or substituted by halogen, C 1  -C 4  alkyl, C 1  -C 4  alkoxy, C 1  -C 4  haloalkyl, nitro or cyano; one of R 3  and R 4  is methoxy; or 
     R 3  and R 4 , together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic ring system which may contain an additional oxygen or sulfur atom in the ring; and the metal or ammonium salts thereof.

CROSS-REFERENCE TO RELATED APPLICATION

This is a continuation-in-part of my application Ser. No. 673,077 filedNov. 19, 1984, now U.S. Pat. No. 4,618,360, which in turn is acontinuation-in-part of my application Ser. No. 610,222 filed May 14,1984, now U.S. Pat. No. 4,584,013.

The present invention relates to novel cyclohexanedionecarboxylic acidderivatives with herbicidal and plant growth regulating properties, tocompositions which contain them, and to the use of said derivatives forselective and total weed control and for regulating plant growth.

The novel cyclohexanedionecarboxylic acid derivatives have the formula I##STR2## wherein A is an --OR₂ or --NR₃ R₄ radical,

R is C₃ -C₆ cycloalkyl,

R₂, R₃ and R₄ are each independently hydrogen, C₁ -C₆ alkyl, C₁ -C₆haloalkyl, C₂ -C₁₀ alkoxyalkyl, C₂ -C₁₀ alkylthioalkyl; C₃ -C₆ alkenylwhich is unsubstituted or substituted by halogen, C₁ -C₄ alkoxy or C₁-C₄ alkylthio; C₃ -C₆ alkynyl; phenyl or C₁ -C₆ aralkyl, wherein thephenyl nucleus is unsubstituted or substituted by halogen, C₁ -C₄ alkyl,C₁ -C₄ alkoxy, C₁ -C₄ haloalkyl, nitro or cyano; one of R₃ and R₄ ismethoxy or

R3 and R₄, together with the nitrogen atom to which they are attached,also form a 5- or 6-membered heterocyclic ring system which may containan additional oxygen or sulfur atom in the ring or a metal or ammoniumsalt thereof.

In the above definitions the alkyl radicals comprise both straight chainand branched radicals, e.g. methyl, ethyl, propyl, isopropyl, butyl,isobutyl, sec-butyl, tert-butyl, as well as all stereoisomers of thehigher homologues. Alkenyl and alkynyl also comprise straight chain andbranched radicals, e.g. vinyl, allyl, methallyl, butenyl, methylbutenyland dimethylbutenyl, ethynyl, propynyl, butynyl, methylbutynyl anddimethylbutynyl.

The cycloalkyl group encompasses cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl.

Halogen is fluorine, chlorine, bromine or iodine.

A 5- or 6-membered heterocyclic ring system --NR₃ R₄ which may containan additional oxygen or sulfur atom in the ring is pyrrole, pyrolidine,piperidine, morpholine or also thiomorpholine. These rings may also besubstituted by methyl.

The salts of these compounds are obtained with bases. Suitable bases arepreferably alkali metal hydroxides, alkaline earth metal hydroxides,iron, copper, nickel and zinc hydroxides, and also ammonia or quaternaryC₁ -C₄ alkylammonium or C₁ -C₄ hydroxyalkylammonium bases.

The cyclohexanedionecarboxylic acid derivatives of the formula I havegood herbicidal and plant growth regulating properties. Particularlyeffective compounds comprise the following groups:

cyclohexane derivatives of the formula I wherein A is an ester rest--OR₂ and the metal and ammonium salts thereof

the derivatives of the formula I, wherein A is an --NR₃ R₄ radical andR, is as defined above, and the metal and ammonium salts thereof.

Preferred individual compounds are:

Ethyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate

ethyl-4-cyclobutanoyl-3,5-cyclohexanedione-1-carboxylate

ethyl-4-cyclopentanoyl-3,5-cyclohexanedione-1-carboxylate

ethyl-4-cyclohexanoyl-3,5-cyclohexanedione-1-carboxylate

methyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate

isopropyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate

isobutyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate

4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate

4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate-tri-n-butylammoniumsalt

4-cyclobutanoyl-3,5-cyclohexanedione-1-carboxylate

4-cyclopentanoyl-3,5-cyclohexanedione-1-carboxylate

4-cyclohexanoyl-3,5-cyclohexanedione-1-carboxylate

dimethyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxamide

dimethyl-4-cyclobutanoyl-3,5-cyclohexanedione-1-carboxamide

benzyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxamide

and the sodium, ammonium and tetramethylammonium salts thereof.

The cyclohexanedionecarboxylic acid derivatives of the formula I can beobtained in different tautomeric forms. For example, methyl4-(cyclopropyl-1-hydroxy-methylidene)-3,5-cyclohexanedione-1-carboxylateis obtained in the following forms: ##STR3##

The cyclohexanedionecarboxylates of the formula I are prepared inconventional manner by reacting a 3,5-cyclohexanedionecarboxylic acidderivative of the formula II ##STR4## wherein A is an ester or amideradical as defined above, with a cycloalkyl-carbonic acid halide of theformula III

    Hal--COR                                                   (III)

wherein R is C₃ -C₆ cycloalkyl in an inert organic solvent and in thepresence of a base as acid acceptor and isolating the product soobtained.

The compounds of formula II react also with their enolic hydroxidegroup. This group has either to be liberated again by acid hydrolysisfrom the condensed --OCOR-rest or else it has to be protected previouslyby etherification e.g. in an acid medium in the presence of a waterabsorber, like concentrated sulfuric acid, distillation on awater-separated fitted preferably with a molecular sieve or withN,N-dicyclohexylcarbonimide.

The preparation of these intermediates is known e.g. from J. Am. Chem.Soc. 78 (1956) 4405 and 81 (1958) 4278 or also from the publishedJapanese Patent Application JA-A No. 57-47947.

Some of these intermediates are new. They correspond to the formula V##STR5## wherein A is defined as above under formula I and R¹¹ isselected from among C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆haloalkenyl, C₃ -C₆ alkinyl, C₂ -C₁₀ alkoxyalkyl and C₂ -C₁₀alkoxyalkenyl and are part of this invention.

Suitable solvents for these reactions are in particular aromatichydrocarbons such as benzene, toluene and xylene, and also halogenatedhydrocarbons such as chloroform, dichloroethane and carbontetrachloride.

The reaction temperatures are in the range from room temperature to theboiling point of the reaction mixture. During the addition of acidchloride it may be necessary to cool the reaction vessel.

Suitable acid acceptors are organic and inorganic bases, e.g. pyridine,4-aminopyridine, collidine, triethylamine, ammonium, and sodium,potassium or calcium carbonate or the corresponding bicarbonates.

Suitable acid halides of the formula III are mainly the chloride of,cycloalkanoic acids such as cyclo butyryl chloride, cyclopentanoylchloride, cyclopropanoyl chloride or cyclohexanoyl chloride, and alsothe corresponding bromides.

The starting cyclohexanedionecarboxylic acid derivatives of the formulaII are obtained on the one hand by hydrogenating 3,5-dihydroxybenzoicacid with hydrogen and Raney nickel and subsequently esterifying oramidating the acid radical in accordance with the following reactionscheme: ##STR6##

In the above reaction the keto group must be protected, e.g. as enolether or enamine, q.v. J. Am. Chem. Soc. 78, 4405 (1956).

However, it is also possible to hydrogenate a 3,5-dihydroxybenzoic acidderivative with hydrogen and Raney nickel in accordance with thereaction scheme: ##STR7## q.v. Arch. Pharm. 307, 577 (1974).

When used at low rates of application, the compounds of formula I havegood growth inhibiting and selective herbicidal properties which makethem most suitable for use in crops of useful plants, especially insugar cane, cereals, cotton, soybeans, maize and rice. In some casesdamage is also caused to weeds which have only been controlled up to nowwith total herbicides.

The mode of action of these compounds is unusual. Many aretranslocatable, i.e. they are absorbed by the plant and transported toother parts of it where they then exert their action. Thus, for example,it is possible to damage perennial weeds to the roots by surfacetreatment. Compared with other herbicides and growth regulators, thenovel compounds of the formula I are effective even when used at verylow rates of application.

In addition the compounds of formula I have pronounced growth-regulatingproperties which can result in an increase in the yield of cultivatedplants or harvested crops. Further, many compounds of formula I have agrowth inhibiting action which is dependent on the concentration. Thegrowth of both monocots and dicots is inhibited. Thus, for example, thecompounds of formula I selectively inhibit the growth of leguminosaewhich are frequently planted as cover crops in tropical regions, sothat, while soil erosion between cultivated plants is prevented, thecover crops cannot compete with the cultivated plants.

Inhibition of the vegetative growth of many cultivated plants permitsmore plants to be sown in a crop area, so that a higher yield may beobtained per unit of area. A further mechanism of yield increase usinggrowth regulators resides in the fact that nutrients are able to promoteflower formation and fruiting to a greater extent, whilst vegetativegrowth is inhibited.

Inhibition of the vegetative growth of monocot plants, e.g. grasses oralso cultivated plants such as cereals, is sometimes desirable andadvantageous. Such a growth inhibition is of economic interest, interalia, in respect of grasses, as the frequency of cutting in flowgardens, parks, sport fields or road shoulders can thereby be reduced.Of importance too is the inhibition of growth of herbaceous and ligneousplants on road shoulders and near transmission lines, or quite generallyin areas in which strong growth is undesirable.

The use of growth regulators for inhibiting the growth in height ofcereals is also important, as shortening the stalks diminishes orcompletely eliminates the danger of lodging before harvesting. Inaddition, growth regulators are able to bring about a strengthening ofthe stalks in crops of cereals and this too counteracts lodging.Further, the compounds of formula I are suitable for preventing storedpotatoes from seeding. During winter storage, potatoes often developsprouts which result in shrinkage, weight loss, and rot.

At higher rates of application, all tested plants are so severelydamaged in their development that they die.

The invention also relates to herbicidal and growth-regulatingcompositions which contain a novel compound of the formula I, and alsoto methods of controlling weeds pre- and postemergence and of inhibitingthe growth of monocots and docots, especially grasses, tropical covercrops and tobacco plant suckers.

The compounds of the formula I are used in unmodified form or,preferably, as compositions together with the adjuvants conventionallyemployed in the art of formulation, and are therefore formulated inknown manner to emulsifiable concentrates, coatable pastes, directlysprayable or dilutable solutions, dilute emulsions, wettable powders,soluble powders, dusts, granulates, and also encapsulations in e.g.polymer substances. As with the nature of the compositions, the methodsof application, such as spraying, atomising, dusting, scattering orpouring, are chosen in accordance with the intended objectives and theprevailing circumstances.

The formulations, i.e. the compositions containing the compound (activeingredient) of the formula I and, where appropriate, a solid or liquidadjuvant, are prepared in known manner, e.g. by homogeneously mixingand/or grinding the active ingredients with extenders, e.g. solvents,solid carriers and, where appropriate, surface-active compounds(surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractionscontaining 8 to 12 carbon atoms, e.g. xylene mixtures or substitutednaphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate,aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols andglycols and their ethers and esters, such as ethanol, ethylene glycol,ethylene glycol monomethyl or monoethyl ether, ketones such ascyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone,dimethylsulfoxide or dimethylformamide, as well as epoxidised vegetableoils such as epoxidised coconut oil or soybean oil; or water.

The solid carriers used e.g. for dusts and dispersible powders arenormally natural mineral fillers such as calcite, talcum, kaolin,montmorillonite or attapulgite. In order to improve the physicalproperties it is also possible to add highly dispersed silicic acid orhighly dispersed absorbent polymers. Suitable granulated adsorptivecarriers are porous types, for example pumice, broken brick, sepioliteor bentonite; and suitable nonsorbent carriers are materials such ascalcite or sand. In addition, a great number of pregranulated materialsof inorganic or organic nature can be used, e.g. especially dolomite orpulverised plant residues.

Depending on the nature of the compound of the formula I to beformulated, suitable surface-active compounds are nonionic, cationicand/or anionic surfactants having good emulsifying, dispersing andwetting properties. The term "surfactants" will also be understood ascomprising mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps andwater-soluble synthetic surface-active compounds.

Suitable soaps are the alkali metal salts, alkaline earth metal salts orunsubstituted or substituted ammonium salts or higher fatty acids (C₁₀-C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, orof natural fatty acid mixtures which can be obtained e.g. from coconutoil or tallow oil. Mention may also be made of fatty acid methyltaurinsalts.

More frequently, however, so-called synthetic surfactants are used,especially fatty sulfonates, fatty sulfates, sulfonated benzimidazolederivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually in the form of alkali metalsalts, alkaline earth metal salts or unsubstituted or substitutedammonium salts and contain a C₈ -C₂₂ alkyl radical which also includesthe alkyl moiety of acyl radicals, e.g. the sodium or calcium salt oflignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcoholsulfates obtained from natural fatty acids. These compounds alsocomprise the salts of sulfuric acid esters and sulfonic acids of fattyalcohol/ethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonic acid groups and one fatty acid radicalcontaining 8 to 22 carbon atoms. Examples of alkylarylsulfonates are thesodium, calcium or triethylanolamine salts of dodecylbenzene sulfonicacid, dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonicacid/formaldehyde condensation product. Also suitable are correspondingphosphates, e.g. salts of the phosphoric acid ester of an adduct ofp-nonylphenol with 4 to 14 moles of ethylene oxide, and phospholipids.

Non-ionic surfactants are preferably polyglycol ether derivatives ofaliphatic or cycloaliphatic alcohols, or saturated or unsaturated fattyacids and alkylphenols, said derivatives containing 3 to 30 glycol ethergroups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moietyand 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts ofpolyethylene oxide with polypropylene glycol, ethylenediamine propyleneglycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms inthe alkyl chain, which adducts contain 20 to 250 ethylene glycol ethergroups and 10 to 100 propylene glycol ether groups. These compoundsusually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of non-ionic surfactants arenonylphenolpolyethoxyethanols, castor oil polyglycol ethers,polypropylene/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitanand polyoxyethylene sorbitan trioleate are also suitable non-ionicsurfactants.

Cationic surfactants are preferably quaternary ammonium salts whichcontain, as N-substituent, at least one C₈ -C₂₂ alkyl radical and, asfurther substituents, lower unsubstituted or halogenated alkyl, benzylor lower hydroxyalkyl radicals. The salts are preferably in the form ofhalides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammoniumchloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation aredescribed e.g. in the following publications:

"McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp.,Ridgewood, N.J., 1981; H. Stache, "Tensid-Taschenbuch", 2nd Edition, C.Hanser Verlag, Munich & Vienna, 1981; M. and J. Ash, "Encyclopedia ofSurfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-81.

The compositions usually contain 0.1 to 95%, preferably 0.1 to 80%, of acompound of the formula I, 1 to 99.9%, of a solid or liquid adjuvant,and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Preferred formulations are composed in particular of the followingconstituents (%=percentage by weight):

    ______________________________________                                        Emulsifiable concentrates                                                     active ingredient:                                                                            1 to 20%, preferably 5 to 10%                                 surfactant:      5 to 30%, preferably 10 to 20%                               liquid carrier: 50 to 94%, preferably 70 to 85%                               Dusts                                                                         active ingredient:                                                                            0.1 to 10%, preferably 0.1 to 1%                              solid carrier:  99.9 to 90%, preferably 99.9 to 99%                           Suspension concentrates                                                       active ingredient:                                                                             5 to 75%, preferably 10 to 50%                               water:          94 to 25%, preferably 90 to 30%                               surfactant:     1 to 40%, preferably 2 to 30%                                 Wettable powders                                                              active ingredient:                                                                            0.5 to 90%, preferably 1 to 80%                               surfactant:     0.5 to 20%, preferably 1 to 15%                               solid carrier:   5 to 95%, preferably 15 to 90%                               Granulates                                                                    active ingredient:                                                                            0.5 to 30%, preferably 3 to 15%                               solid carrier:  99.5 to 70%, preferably 97 to 85%.                            ______________________________________                                    

Whereas commercial products will be preferably formulated asconcentrates, the end user will normally employ dilute formulations. Theformulations can be diluted to a concentration as low as 0.001% Therates of application are normally from 0.01 to 10 kg a.i./ha, preferablyfrom 0.025 to 5 kg a.i./ha.

The compositions may also contain further auxiliaries such asstabilisers, antifoams, viscosity regulators, binders, tackifiers, aswell as fertilisers and other compounds for obtaining special effects.

The invention is illustrated by the following Examples.

PREPARATORY EXAMPLES Example 1: Preparation of isobutyl4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate ##STR8##

(a) Isobutyl 3,5-cyclohexanedionecarboxylate

A mixture of 50 g of 3,5-cyclohexanedione-1-carboxylic acid, 150 ml ofisobutanol, 30 g of 85% orthophosphoric acid and 400 ml of toluene isboiled overnight in a water separator. The solution is then concentratedin a rotovap. The residue is taken up in 200 ml of tetrahydrofuran, andthe solution is boiled for 2 hours after addition of 100 ml of 1Nhydrochloric acid. The cooled solution is extracted with ethyl acetateand the organic phase is separated, washed with a saturated solution ofsodium chloride, dried and concentrated. The wax-like residue isrecrystallised from ether/hexane and the crystalline product melts at74°-76° C.

(b) Isobutyl 4-cyclopropionyl-3,5-cyclohexanedione-1-carboxylate

30 ml of cyclopropanoyl chloride are added dropwise to a solution of 60g of isobutyl 3,5-cyclohexanedionecarboxylate and 25 ml of pyridine in400 ml of dichloroethane, and the mixture is stirred for a further 15hours at room temperature. The reaction solution is then filtered andthe filtrate is washed with 1N hydrochloric acid, dried andconcentrated. The O-acylated product so obtained is taken up in 200 mlof dichloroethane, 4 g of 4-dimethylaminopyridine are added, and thereaction mixture is refluxed for 4 hours. The cooled reaction solutionis then washed with 1N hydrochloric acid, dried, concentrated, and theresidue is chromatographed over a small amount of silica gel, affording51 g of isobutyl 4-cyclopropanoyl-3,5-cyclohexanedionecarboxylate as apale oil with a refractive index of n_(D) ²¹ 1.4907.

The following compounds are prepared by procedures analogous to thosedescribed in the foregoing Examples: ##STR9##

                  TABLE 1                                                         ______________________________________                                        No.    OR.sub.2      R           Physical data                                ______________________________________                                        1.01  OC.sub.2 H.sub.5                                                                            cyclopropyl  n.sub.D.sup.30 1.5350                        1.02  OC.sub.2 H.sub.5                                                                            cyclobutyl   m.p. 60-61°                           1.03  OC.sub.2 H.sub.5                                                                            cyclopentyl  Oel                                          1.04  OC.sub.2 H.sub.5                                                                            cyclohexyl   Oel                                          1.05  OCH.sub.3     cyclopropyl  m.p. 60-64°                           1.06  OCH.sub.3     cyclobutyl                                                1.07  OCH.sub.3     cyclopentyl                                               1.08  OCH.sub.3     cyclohexyl                                                1.09  OC.sub.3 H.sub.7 --n                                                                        cyclopropyl                                               1.10  OC.sub.3 H.sub.7 --n                                                                        cyclobutyl                                                1.11  OC.sub.3 H.sub.7 --n                                                                        cyclopentyl                                               1.12  OC.sub.3 H.sub.7 --n                                                                        cyclohexyl                                                1.13  OC.sub.6 H.sub.12 --n                                                                       cyclopropyl                                               1.14  OC.sub.6 H.sub.12 --n                                                                       cyclobutyl                                                1.15  OC.sub.6 H.sub.12 --n                                                                       cyclopentyl                                               1.16  OC.sub.6 H.sub.12 --n                                                                       cyclohexyl                                                1.17  OC.sub.4 H.sub.9 --n                                                                        cyclopropyl                                               1.18  OC.sub.4 H.sub.9 --n                                                                        cyclobutyl                                                1.19  OC.sub.4 H.sub.9 --n                                                                        cyclopentyl                                               1.20  OC.sub.4 H.sub.9 --n                                                                        cyclohexyl                                                1.21  OCH(CH.sub.3).sub.2                                                                         cyclopropyl  m.p. 70-72°                           1.22  OCH(CH.sub.3).sub.2                                                                         cyclobutyl                                                1.23  OCH(CH.sub.3).sub.2                                                                         cyclopentyl                                               1.24  OCH(CH.sub. 3).sub.2                                                                        cyclohexyl                                                1.25  OC.sub.4 H.sub.9 iso                                                                        cyclopropyl  n.sub.D.sup.21 1.4907                        1.26  OC.sub.4 H.sub.9 iso                                                                        cyclobutyl                                                1.27  OC.sub.4 H.sub.9 iso                                                                        cyclopentyl                                               1.28  OC.sub.4 H.sub.9 iso                                                                        cyclohexyl                                                1.29  OC.sub.4 H.sub.9 tert                                                                       cyclopropyl                                               1.30  OC.sub.4 H.sub.9 tert                                                                       cyclobutyl                                                1.31  OC.sub.4 H.sub.9 tert                                                                       cyclopentyl                                               1.32  OC.sub.4 H.sub.9 tert                                                                       cyclohexyl                                                1.33  OCH.sub.2 CH═CH.sub.2                                                                   cyclopropyl                                               1.34  OCH.sub.2 CH═CH.sub.2                                                                   cyclobutyl                                                1.35  OCH.sub.2 CH═CH.sub.2                                                                   cyclopentyl                                               1.36  OCH.sub.2 CH═CH.sub.2                                                                   cyclohexyl                                                1.37  OCH.sub.2 C═CH                                                                          cyclopropyl                                               1.38  OCH.sub.2 C═CH                                                                          cyclobutyl                                                1.39  OCH.sub.2 C═CH                                                                          cyclopentyl                                               1.40  OCH.sub.2 C═CH                                                                          cyclohexyl                                                1.41  OC.sub.2 H.sub.4 OCH.sub.3                                                                  cyclopropyl                                               1.42  OC.sub.2 H.sub.4 OCH.sub.3                                                                  cyclobutyl                                                1.43  OC.sub.2 H.sub.4 OCH.sub.3                                                                  cyclopentyl                                               1.44  OC.sub.2 H.sub.4 OCH.sub.3                                                                  cyclohexyl                                                1.45  OC.sub.2 H.sub.4 SCH.sub.3                                                                  cyclopropyl                                               1.46  OC.sub.2 H.sub.4 SCH.sub.3                                                                  cyclobutyl                                                1.47  OC.sub.2 H.sub.4 SCH.sub.3                                                                  cyclopentyl                                               1.48  OC.sub.2 H.sub.4 SCH.sub.3                                                                  cyclohexyl                                                1.49  benzyloxy     cyclopropyl                                               1.50  benzyloxy     cyclobutyl                                                1.51  benzyloxy     cyclopentyl                                               1.52  benzyloxy     cyclohexyl                                                1.53  OC.sub.2 H.sub.4 Cl                                                                         cyclopropyl                                               1.54  OC.sub.2 H.sub.4 Cl                                                                         cyclobutyl                                                1.55  OC.sub.2 H.sub.4 Cl                                                                         cyclopentyl                                               1.56  OC.sub.2 H.sub.4 Cl                                                                         cyclohexyl                                                1.57  OC.sub.3 H.sub.6 Cl                                                                         cyclopropyl                                               1.58  OC.sub.3 H.sub.6 Cl                                                                         cyclobutyl                                                1.59  OC.sub.3 H.sub.6 Cl                                                                         cyclopentyl                                               1.60  OC.sub.3 H.sub.6 Cl                                                                         cyclohexyl                                                1.61  OCH.sub.2 OCH.sub.3                                                                         cyclopropyl                                               1.62  OCH.sub.2 OCH.sub.3                                                                         cyclobutyl                                                1.63  OCH.sub.2 OCH.sub.3                                                                         cyclopentyl                                               1.64  OCH.sub.2 OCH.sub.3                                                                         cyclohexyl                                                1.65  OCH.sub.3     1-methylcyclo-                                                                propyl                                                    1.66  OC.sub.2 H.sub.5                                                                            1-methylcyclo-                                                                propyl                                                    1.67  OC.sub.2 H.sub.9 --n                                                                        1-methylcyclo-                                                                propyl                                                    1.68  OCH.sub.2 CH═CH.sub.2                                                                   1-methylcyclo-                                                                propyl                                                    1.69  benzyloxy     1-methylcyclo-                                                                propyl                                                    1.70  OC.sub.2 H.sub.4 OCH.sub.3                                                                  1-methylcyclo-                                                                propyl                                                    1.71  OCH.sub.3     4,4-Diemthyl-                                                                 cyclohexyl                                                1.72  OC.sub.2 H.sub.5                                                                            4,4-Dimethyl-                                                                 cyclohexyl                                                1.73  OC.sub.4 H.sub.9 --n                                                                        4,4-Dimethyl-                                                                 cyclohexyl                                                1.74  OCH.sub.2 CH═CH.sub.2                                                                   4,4-Diemthyl-                                                                 cyclohexyl                                                1.75  benzyloxy     4,4-Dimethyl-                                                                 cyclohexyl                                                1.76  OC.sub.2 H.sub.4 OCH.sub.3                                                                  4,4-Dimethyl-                                                                 cyclohexyl                                                1.77  OH            cyclopropyl  m.p. 142-146°                         1.78  OH            cyclobutyl                                                1.79  OH            cyclopentyl   m.p. 95-103°                         1.80  OH            cyclohexyl   m.p. 155-158°                         1.81  OH            cyclopropyl  tri-n-butyl-                                                                  ammonium salt,                                                                oil                                          ______________________________________                                         ##STR10##

                  TABLE 2                                                         ______________________________________                                        No.   NR.sub.3 R.sub.4                                                                              R           Physical data                               ______________________________________                                        2.01  NH.sub.2       cyclopropyl                                              2.02  NH.sub.2       cyclobutyl                                               2.03  NH.sub.2       cyclopentyl                                              2.04  NH.sub.2       cyclohexyl                                               2.05  NHCH.sub.3     cyclopropyl                                              2.06  NHCH.sub.3     cyclobutyl                                               2.07  NHCH.sub.3     cyclopentyl                                              2.08  NHCH.sub.3     cyclohexyl                                               2.09  N(CH.sub.3).sub.2                                                                            cyclopropyl  m.p. 109-112°                        2.10  N(CH.sub.3).sub.2                                                                            cyclobutyl   m.p. 72-78°                          2.11  N(CH.sub.3).sub.2                                                                            cyclopentyl                                              2.12  N(CH.sub.3).sub.2                                                                            cyclohexyl                                               2.13  N(CH.sub.3)OCH.sub.3                                                                         cyclopropyl                                              2.14  N(CH.sub.3)OCH.sub.3                                                                         cyclobutyl                                               2.15  N(CH.sub.3)OCH.sub.3                                                                         cyclopentyl                                              2.16  N(CH.sub.3)OCH.sub.3                                                                         cyclohexyl                                               2.17  NHCH.sub.2 CH═CH.sub.2                                                                   cyclopropyl                                              2.18  NHCH.sub.2 CH═CH.sub.2                                                                   cyclobutyl                                               2.19  NHCH.sub.2 CH═CH.sub.2                                                                   cyclopentyl                                              2.20  NHCH.sub.2 CH═CH.sub.2                                                                   cyclohexyl                                               2.21  N(CH.sub.2 CH═CH.sub.2).sub.2                                                            cyclopropyl                                              2.22  N(CH.sub.2 CH═CH.sub.2).sub.2                                                            cyclobutyl                                               2.23  N(CH.sub.2 CH═CH.sub.2).sub.2                                                            cyclopentyl                                              2.24  N(CH.sub.2 CH═CH.sub.2).sub.2                                                            cyclohexyl                                               2.25  N(CH.sub.3)C.sub.2 H.sub.5                                                                   cyclopropyl                                              2.26  N(CH.sub.3)C.sub.2 H.sub.5                                                                   cyclobutyl                                               2.27  N(CH.sub.3)C.sub.2 H.sub.5                                                                   cyclopentyl                                              2.28  N(CH.sub.3)C.sub.2 H.sub.5                                                                   cyclohexyl                                               2.29  benzylamino    cyclopropyl  m.p. 130-144°                        2.30  benzylamino    cyclobutyl                                               2.31  benzylamino    cyclopentyl                                              2.32  benzylamino    cyclohexyl                                               2.33  anilino        cyclopropyl                                              2.34  anilino        cyclobutyl                                               2.35  anilino        cyclopentyl                                              2.36  anilino        cyclohexyl                                               2.37  4-chloranilino cyclopropyl                                              2.38  4-chloranilino cyclobutyl                                               2.39  4-chloranilino cyclopentyl                                              2.40  4-chloranilino cyclohexyl                                               2.41  3-trifluormethyl-                                                                            cyclopropyl                                                    anilino                                                                 2.42  3-trifluormethyl-                                                                            cyclobutyl                                                     anilino                                                                 2.43  3-trifluormethyl-                                                                            cyclopentyl                                                    anilino                                                                 2.44  3-trifluormethyl-                                                                            cyclohexyl                                                     anilino                                                                 2.45  4-methoxyanilino                                                                             cyclopropyl                                              2.46  4-methoxyanilino                                                                             cyclobutyl                                               2.47  4-methoxyanilino                                                                             cyclopentyl                                              2.48  4-methoxyanilino                                                                             cyclohexyl                                               2.49  pyrrolinyl     cyclopropyl                                              2.50  pyrrolinyl     cyclobutyl                                               2.51  pyrrolinyl     cyclopentyl                                              2.52  pyrrolinyl     cyclohexyl                                               2.53  cyclopropylamino                                                                             cyclopropyl                                              2.54  cyclopropylamino                                                                             cyclobutyl                                               2.55  cyclopropylamino                                                                             cyclopentyl                                              2.56  cyclopropylamino                                                                             cyclohexyl                                               2.57  NHC.sub.6 H.sub.13 n                                                                         1-methylcyclo-                                                                propyl                                                   2.58  NHC.sub.2 H.sub.4 SCH.sub.3                                                                  4,4-dimethyl-                                                                 cyclohexyl                                               2.59  N--methylbenzyl-                                                                             4,4-dimethyl-                                                  amino          cyclohexyl                                               2.60  anilino        1-methylcyclo-                                                                propyl                                                   2.61  NHC.sub.6 H.sub.13 n                                                                         1-methylcyclo-                                                                propyl                                                   2.62  NHC.sub.2 H.sub.4 SCH.sub.3                                                                  3,5-dimethyl-                                                                 cyclohexyl                                               ______________________________________                                    

In Example 1a, there is prepared an intermediate product. According tothis example the following compounds are prepared ##STR11##

                  TABLE 3                                                         ______________________________________                                        No.    A             R.sub.2    Physical data                                 ______________________________________                                        3.01   N(CH.sub.3).sub.2                                                                           CH.sub.3   oil                                           3.02   N(CH.sub.3).sub.2                                                                           H          m.p. 152-155°                          3.03   benzoyloxy    H                                                        3.04   4-chlorobenzyloxy                                                                           H                                                        3.05   CH.sub.3 OC.sub.2 H.sub.4 O                                                                 H                                                        3.06   4-benzylamino H                                                        3.07   anilino       H                                                        3.08   anilino       CH.sub.3                                                 3.09   (CH.sub.3).sub.2 CHCH.sub.2 --                                                              CH.sub.3   oil                                           3.10   (CH.sub.3).sub.2 CHCH.sub.2 NH                                                              H                                                        3.11   (C.sub.2 H.sub.5).sub.2 N                                                                   H          oil                                           3.12   1-methylanilino                                                                             CH.sub.3                                                 3.13   1-methylanilino                                                                             H          m.p. 143-145°                          3.14   (CH.sub.2 ═CHCH.sub.2).sub.2 N                                                          CH.sub.3   oil                                           3.15   (CH.sub.2 ═CHCH.sub.2).sub.2 N                                                          H          resin                                         3.16   piperidino    CH.sub.3                                                 3.17   piperidino    H                                                        3.18   CH.sub.3 SC.sub.2 H.sub.4 NH                                                                CH.sub.3                                                 3.19   CH.sub.3 SC.sub.2 H.sub.4 NH                                                                H          resin                                         3.20   HSC.sub.2 H.sub.4 NH                                                                        CH.sub.3   wax                                           3.21   HSC.sub.2 H.sub.4 NH                                                                        H                                                        3.22   H.sub.5 C.sub.3 (CH.sub.3)CHO                                                               H           m.p. 76-78°                           ______________________________________                                    

Example 2 Formulation Examples for compounds of the formula I ormixtures thereof with herbicides

    ______________________________________                                        (a) Wettable powders (a)     (b)     (c)                                      ______________________________________                                        Compound of Table 1 or 2                                                                           20%     60%      0.5%                                    sodium lignosulfonate                                                                              5%      5%        5%                                     sodium laurylsulfate 3%      --      --                                       sodium diisobutylnaphahalenesulfonate                                                              --      6%        6%                                     octylphenol polyethylene glycol ether                                                              --      2%        2%                                     (7-8 moles of ethylene oxide)                                                 highly dispersed silicic acid                                                                      5%      27%       27%                                    kaolin               67%     --      --                                       sodium chloride      --      --      59.5%                                    ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders which can be diluted with water to give suspensions of thedesired concentration.

    ______________________________________                                        (b) Emulsifiable concentrates                                                                        (a)    (b)                                             ______________________________________                                        Compound of Table 1 or 2                                                                             10%    1%                                              octylphenol polyethylene glycol ether                                                                 3%    3%                                              (4-5 moles of ethylene oxide)                                                 calcium dodecylbenzenesulfonate                                                                       3%    3%                                              castor oil polyglycol ether                                                                           4%    4%                                              (36 moles of ethylene oxide)                                                  cyclohexanone          30%    10%                                             xylene mixture         50%    79%                                             ______________________________________                                    

Emulsions of any required concentration can be obtained from thisconcentrate by dilution with water.

    ______________________________________                                        (c) Dusts           (a)     (b)                                               ______________________________________                                        Compound of Table 1 or 2                                                                           0.1%    1%                                               talcum              99.9%   --                                                kaolin              --      99%                                               ______________________________________                                    

Dusts which are ready for use are obtained by mixing the activeingredient with the carriers, and grinding the mixture in a suitablemill.

    ______________________________________                                        (d) Extruder granulate                                                                            (a)    (b)                                                ______________________________________                                        Compound of Table 1 or 2                                                                          10%    1%                                                 sodium lignosulfonate                                                                              2%    2%                                                 carboxymethylcellulose                                                                             1%    1%                                                 kaolin              87%    96%                                                ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and themixture is subsequently moistened with water. The mixture is extrudedand then dried in a stream of air.

    ______________________________________                                        (e) Coated granulate                                                          ______________________________________                                        Compound of Table 1 or 2                                                                          3%                                                        polyethylene glycol 200                                                                           2%                                                        kaolin              94%                                                       ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coatedgranulates are obtained in this manner.

    ______________________________________                                        (f) Suspension concentrate                                                                           (a)     (b)                                            ______________________________________                                        Compound of Table 1 or 2                                                                             40%     5%                                             ethylene glycol        10%     10%                                            nonylphenol polyethylene glycol ether                                                                 6%     1%                                             (15 moles of ethylene oxide)                                                  sodium lignosulfonate  10%     5%                                             carboxymethylcellulose  1%     1%                                             37% aqueous formaldehyde solution                                                                    0.2%    0.2%                                           silicone oil in the form of a 75%                                                                    0.8%    0.8%                                           aqueous emulsion                                                              water                  32%     77%                                            ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired concentration can be obtained by dilution with water.

    ______________________________________                                        (g) Salt solution                                                             ______________________________________                                        Compound of Table 1 or 2                                                                             5%                                                     isopropylamine         1%                                                     octylphenol polyethylene glycol ether                                                                3%                                                     (78 moles of ethylene oxide)                                                  water                  91%                                                    ______________________________________                                    

Example 3: Preemergence herbicidal activity

Plant seeds are sown in flower pots (diameter 11 cm) in a greenhouse.Immediately afterwards the surface of the soil is treated with anaqueous emulsion of the test compound at a concentration of 4 kg a.i.per hectare. The pots are then kept in the greenhouse at a temperatureof 22°-25° C. and 50 to 70% relative humidity. The test is evaluated 3weeks later by assessing the condtions of plants. The tested compoundsof Tables 1 and 2 damage most of the test plants.

Example 4: Postemergence herbicidal activity

Different cultivated plants and weeds are reared from seeds in pots in agreenhouse until they have reached the 4- to 6-leaf stage. The plantsare sprayed with an aqueous emulsion of test compound (prepared from a25% emulsifiable concentrate) at a concentration of 4 kg/ha. The treatedplants are then kept under optimum conditions of light, regularwatering, temperature (22°-25° C.), and relative humidity (50-70%). Thetest is evaluated 15 days. The tested compound of Tables 1 and 2 damagemost of the plants.

Example 5: Growth inhibition of tropical cover crops

Cuttings from the test plants Phosphocarpus palustris and Centrosemapubescens are reared in plastic pots that are filled with a 1:3earth-peat mixture. When the plants grow roots they are replanted intopots of 11 cm diameter and watered as necessary.

The test plants are kept at 70% relative humidity and 6000 luxartificial light for 14 hours per day, at day temperatures of 27° C. andnight temperatures of 21° C. The fully grown test plants are cut back toa height of 15 cm. The plants are sprayed 7 days later with an aqueousemulsion or suspension of the test compounds. The test is evaluated 4weeks after the treatment and the new growth is measured and compared tothat of untreated plants which have been out back the same day.

The results are as follows:

    ______________________________________                                                     new growth                                                       amount         Phosphocarpus                                                                              Centrosema                                        compound                                                                              applied    weight  length weight                                                                              length                                ______________________________________                                        1.01     300 g/ha  87%     100%   87%   100%                                          1000 g/ha  74%     100%   61%   20%                                           3000 g/ha  32%      20%   61%   10%                                   1.02     300 g/ha  90%     100%   87%   100%                                          1000 g/ha  71%      80%   74%   90%                                           3000 g/ha  52%      30%   65%   10%                                   none    --         100%    100%   100%  100%                                  control                                                                       ______________________________________                                    

Example 6: Growth regulation of soybeans

Soybeans of the "Williams" variety are sown in plastic containers (20×20cm) in an earth/peat/sand mixture (6:3:1). The containers are put into aclimatic chamber and the plants develop to the beginning of theflowering stage after about 7 weeks by optimum control of temperature,light, fertiliser addition, and watering. The plants are then sprayedwith an aqueous mixture of a compound to be tested until thoroughlywetted. The rate of application corresponds to 1000 g of activeingredient and 500 l of water per hectare. Evaluation is made about 4weeks after application.

The quantitative growth after application of the test-substance and theyield giving criteria are compared with those of not treated controlplants. The substances clearly reduce the linear growth withoutdiminishing the yield. They markedly increase the number and weight ofthe harvested siliques on the leading shoot.

The results for compound 1.01, which was applied at 1000 g/ha are asfollows (compared with those of not treated plants=100%)

    ______________________________________                                        height of plant        82%                                                    linear growth after applications                                                                     46%                                                    siliques on secondary shoots number                                                                  87%                                                    siliques on secondary shoots weight                                                                  88%                                                    siliques on main shoot number                                                                        106%                                                   siliques on main shoot weight                                                                        103%                                                   phytotoxic symptoms on treated plant                                                                 none                                                   phytotoxic symptoms on new growth                                                                    none                                                   (after treatment)                                                             ______________________________________                                    

other results were as follows:

    ______________________________________                                                     growth after treatment                                            compound                                                                              rateapplication                                                                          length %                                                                               weight %                                                                             ##STR12##                                 ______________________________________                                        1.01    1000 g/ha  46       91     1.97                                       1.05     500 g/ha  100      95     1.05                                               1300 g/ha  97       57     1.70                                       1.21     500 g/ha  97       78     1.24                                               1500 g/ha  94       72     1.31                                       1.77     500 g/ha  100      95     1.05                                               1500 g/ha  89       33     2.70                                       1.79     500 g/ha  100      63     1.59                                               1500 g/ha  80       21     3.81                                       1.80     500 g/ha  95       79     1.20                                               1500 g/ha  98       42     2.33                                       1.81     500 g/ha  100      90     1.11                                               1500 g/ha  92       62     1.48                                       control --         100      100    1.00                                       ______________________________________                                    

Example 7: Growth inhibition of cereals

Summer barley (Hordeum vulgare) and summer wheat (Triticum) are sown insterilised soil in plastic beakers in a greenhouse and watered asrequired. The cereal shoots are treated about 21 days after sowing withan aqueous spray mixture of a compound of the formula I. Theconcentration corresponds to 3 kg of active ingredient per hectare.Evaluation of the growth of the cereals is made 28 days afterapplication. A comparison with untreated controls shows that the growthof cereal plants treated with the test compounds is significantlyreduced (controls=100%) and that the diameter of the stalks has in somecases increased. The inhibition of the linear growth is without greatinfluence of the weight of the plant. The plant is small and sturdy andless apt for laying down because of rain and wind.

The results are as follows:

    __________________________________________________________________________                barley              wheat                                                             dry  new growth     dry  new growth                             application                                                                         circumference                                                                         weight                                                                             after  circumference                                                                         weight                                                                             after                            compound                                                                            rate  stalk   of shoot                                                                           treatment                                                                            stalk   of shoot                                                                           treatment                        __________________________________________________________________________    1.01   300 g/ha                                                                           106     83   72      92     88   82                                     1000 g/ha                                                                           110     65   45     104     70   47                                     3000 g/ha                                                                           144     63   17     112     66    8                               1.02   300 g/ha                                                                           115     93   74     106     96   97                                     1000 g/ha                                                                            97     69   68     100     85   88                                     3000 g/ha                                                                           120     59   26      98     69   38                               1.03   300 g/ha                                                                           106     86   94     105     106  96                                     1000 g/ha                                                                           104     84   89      95     92   75                                     3000 g/ha                                                                           110     64   34     107     69   36                               1.04   300 g/ha                                                                            97     84   94     100     102  93                                     1000 g/ha                                                                           103     64   94     102     80   82                                     3000 g/ha                                                                           109     92   70      96     89   54                               1.05   300 g/ha                                                                           100     82   78     109     100  84                                     1000 g/ha                                                                           114     66   53     109     84   58                                     3000 g/ha                                                                           129     57     2    130     64    6                               1.77   300 g/ha                                                                            89     72   60     107     82   45                                     1000 g/ha                                                                           125     53   16     116     73   16                                     3000 g/ha                                                                           118     64    4     147     66    0                               1.80   300 g/ha                                                                           106     88   79      96     77   72                                     1000 g/ha                                                                           123     79   55     100     77   52                                     3000 g/ha                                                                           137     56    9     132     68    7                               control                                                                             --    100     100  100    100     100  100                              __________________________________________________________________________

Example 8: Growth inhibition of grasses and clover

Seeds of the grasses Lolium perenne, Poa pratensis, Festuca rubra,Festuca ovina Dactylis glomerata Cynosurus cristatus, Agropyron repens,Bromus inermis and of two kinds of clover are sown in plastic dishesfilled with an earth/peat/sand mixture (6:3:1), in a greenhouse, andwatered as required. The emergent grasses are cut back weekly to aheight of 4 cm, for about 6 weeks after sowing. 1 day after the lastcut, the grass-mixture is sprayed with an aqueous spray of a compound tobe tested. The concentration of test compound corresponds to a rate ofapplication of 0.3 to 3 kg per hectare. The growth of the grasses isevaluated 21 days after application. The new growth is compared withthat of untreated controls (100%).

The results are as follows:

    ______________________________________                                                application rate                                                      compound  300 g/ha    1000 g/ha 3000 g/ha                                     ______________________________________                                        1.01      77%         37%       31%                                           1.02      74%         51%       43%                                           1.03      66%         66%       41%                                           1.04      79%         76%       66%                                           1.05      88%         67%       36%                                           1.21      80%         51%       29%                                           1.77      76%         61%       45%                                           1.79      74%         59%       35%                                           1.80      82%         62%       65%                                           1.81      81%         50%       42%                                           control   100%        100%      100%                                          ______________________________________                                    

Example 9

Growth-inhibiting test in the greenhouse. Plants of oats (avena sativa),Setaria italica, Lolium perenne, tomatoe (solanum lycopersicum) Sinapsisalba Steallaria media and beans (Phaseolus vulgaris) were raised inplastic pots of 12 cm diameter in the greenhouse. Two weeks, aftersowing the plantlets were sprayed with the diluted concentrate of thesubstance to be tested in an amount that corresponds to 4 kg of activesubstance per hectare. One set of plants was left untreated to serve ascontrol. The test was evaluated two weeks after application of the testsubstance. The length of the growth since application was measured andcalculated in % of that of the untreated control plants (=100% growth).

The results are as follows:

    ______________________________________                                        compound      untreated control                                                                            2.09   2.10                                      ______________________________________                                                      % growth since application                                      plants        of test compound                                                Avena sativa  100            63     38                                        Setaria italica                                                                             100            63     38                                        Lolium perenne                                                                              100            87     87                                        Solanum lycopersicum                                                                        100            38     63                                        Sinapsis alba 100            38     63                                        Stellaria media                                                                             100            63     38                                        Phaseolus vulgaris                                                                          100            13     100                                       ______________________________________                                    

What is claimed is:
 1. A cyclohexanedionecarboxylic acid derivative ofthe formula I ##STR13## wherein A is an --OR₂ or --NR₃ R₄ radical,R isC₃ -C₆ cycloalkyl, R₂, R₃ and R₄ are each independently hydrogen, C₁ -C₆alkyl, C₁ -C₆ haloalkyl, C₁ -C₁₀ alkoxyalkyl, C₂ -C₁₀ alkylthioalkyl; C₃-C₆ alkenyl which is unsubstituted or substituted by halogen, C₁ -C₄alkoxy or C₁ -C₄ alkylthio; C₃ -C₆ alkynyl; phenyl or C₁ -C₆ aralkyl,wherein the phenyl nucleus is unsubstituted or substituted by halogen,C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkyl, nitro or cyano; one of R₃and R₄ is methoxy; or R₃ and R₄, together with the nitrogen atom towhich they are attached, form a 5- or 6-membered heterocyclic ringsystem which may contain an additional oxygen or sulfur atom in thering; and the metal or ammonium salts thereof.
 2. Acyclohexanedionecarboxylic acid derivative according to claim 1, whereinA is an OR₂ radical, R is C₃ -C₆ cycloalkyl and R₂ is hydrogen, C₁ -C₆alkyl, C₁ -C₆ haloalkyl, C₂ -C₁₀ alkoxyalkyl, C₂ -C₁₀ alkylthioalkyl; C₃-C₆ alkenyl, which is unsubstituted or substituted by halogen, C₁ -C₄alkoxy or C₁ -C₄ alkylthio; C₃ -C₆ alkynyl; phenyl or C₁ -C₆ aralkyl,wherein the phenyl nucleus is unsubstituted, or substituted by halogen,C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkyl, nitro or cyano.
 3. Acyclohexanedioncarboxylic acid derivative according to claim 1, whereinA is an --NR₃ R₄ radical, R is C₃ -C₆ cycloalkyl, and R₃ and R₄ are eachindependently hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₁₀alkoxyalkyl, C₂ -C₁₀ alkylthioalkyl; C₃ -C₆ alkenyl, which isunsubstituted or substituted by halogen, C₁ -C₄ alkoxy or C₁ -C₄alkylthio; C₃ -C₆ alkynyl, phenyl or C₁ -C₆ aralkyl, wherein the phenylnucleus is unsubstituted or substituted by halogen, C₁ -C₄ alkyl, C₁ -C₄alkoxy, C₁ -C₄ haloalkyl nitro or cyano; one of R₃ and R₄ is methoxy; orR₃ and R₄, together with the nitrogen atom, to which they are attached,form a 5- or 6-membered heterocyclic ring system, which may contain anadditional oxygen or sulfur atom in the ring. 4.Ethyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate, according toclaim
 1. 5. Ethyl-4-cyclobutanoyl-3,5-cyclohexanedione-1-carboxylate,according to claim
 1. 6.Ethyl-4-cyclopentanoyl-3,5-cyclohexanedione-1-carboxylate, according toclaim
 1. 7. Ethyl-4-cyclohexanoyl-3,5-cyclohexanedione-1-carboxylate,according to claim
 1. 8.Methyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate, according toclaim
 1. 9.Isopropyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate, accordingto claim
 1. 10.Isobutyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate, accordingto claim
 1. 11. 4-Cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate,according to claim
 1. 12.4-Cyclopropanoyl-3,5-cyclohexanedione-1-carboxylate-tri-n-butylammoniumsalt, according to claim
 1. 13.4-Cyclobutanoyl-3,5-cyclohexanedione-1-carboxylate, according toclaim
 1. 14. 4-Cyclopentanoyl-3,5-cyclohexanedione-1-carboxylate,according to claim
 1. 15.4-Cyclohexanoyl-3,5-cyclohexanedione-1-carboxylate, according toclaim
 1. 16.Dimethyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxamide, accordingto claim
 1. 17.Dimethyl-4-cyclobutanoyl-3,5-cyclohexanedione-1-carboxamide, accordingto claim
 1. 18.Benzyl-4-cyclopropanoyl-3,5-cyclohexanedione-1-carboxamide, according toclaim
 1. 19. A composition, which contains as active ingredient aherbicidal and plant-growth regulating effective amount of acyclohexanedionecarboxylic acid derivative according to claim 1,together with an inert carrier and/or other inert formulationassistants.
 20. A method of selectively controlling weeds pre- orpostemergence in crops of useful plants, which comprises applying tosaid useful plants or to the locus thereof an effective amount of acyclohexanedionecarboxylic acid derivative of the formula I ##STR14##wherein A is an --OR₂ or --NR₃ R₄ radical,R is C₃ -C₆ cycloalkyl. R₂, R₃and R₄ are each independently hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl,C₂ -C₁₀ alkoxyalkyl, C₂ -C₁₀ alkylthioalkyl; C₃ -C₆ alkenyl which isunsubstituted or substituted by halogen, C₁ -C₄ alkoxy or C₁ -C₄alkylthio; C₃ -C₆ alkynyl; phenyl or C₁ -C₆ aralkyl, wherein the phenylnucleus is unsubstituted or substituted by halogen, C₁ -C₄ alkyl, C₁ -C₄alkoxy, C₁ -C₄ haloalkyl, nitro or cyano; one of R₃ and R₄ is methoxy;or R₃ and R₄, together with the nitrogen atom to which they areattached, form a 5- or 6-membered heterocyclic ring system which maycontain an additional oxygen or sulfur atom in the ring; and the metalor ammonium salts thereof.
 21. The method of claim 20 wherein the weedsare grasses.
 22. The method of claim 20 wherein the crops of usefulplants are sugar cane, cereals, maize, soya beans, rice and cotton. 23.A method of regulating growth of useful crops plants, which comprisestreating said plants, parts of plants or seeds with an effective amountof a cyclohexanedionecarboxylic acid derivative of the formula I##STR15## wherein A is an --OR₂ or --NR₃ R₄ radical,R is C₃ -C₆cycloalkyl, R₂, R₃ and R₄ are each independently hydrogen, C₁ -C₆ alkyl,C₁ -C₆ haloalkyl, C₂ -C₁₀ alkoxyalkyl, C₂ -C₁₀ alkylthioalkyl; C₃ -C₆alkenyl which is unsubstituted or substituted by halogen, C₁ -C₄ alkoxyor C₁ -C₄ alkylthio; C₃ -C₆ alkynyl; phenyl or C₁ -C₆ aralkyl, whereinthe phenyl nucleus is unsubstituted or substituted by halogen, C₁ -C₄alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkyl, nitro or cyano; one of R₃ and R₄is methoxy; or R₃ and R₄, together with the nitrogen atom to which theyare attached, form a 5- or 6-membered heterocyclic ring system which maycontain an additional oxygen or sulfur atom in the ring; and the metalor ammonium salts thereof.
 24. A method of regulating plant growth ofcereals and soybeans to obtain an increase in yield, which comprisesapplying to said plants an effective amount of acyclohexanedionecarboxylic acid derivative of the formula I according toclaim 23, or of a composition containing said derivative.
 25. A methodof claim 23 of inhibiting plant growth beyond the 2-leaf stage oftropical cover plants, which comprises applying to said plants aneffective amount of the cyclohexanedionecarboxylic acid derivative or ofa composition containing said derivative.